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WO2012075093A2 - Formes galéniques topiques utilisables en vue de l'administration d'acides gras oméga-3 - Google Patents

Formes galéniques topiques utilisables en vue de l'administration d'acides gras oméga-3 Download PDF

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Publication number
WO2012075093A2
WO2012075093A2 PCT/US2011/062559 US2011062559W WO2012075093A2 WO 2012075093 A2 WO2012075093 A2 WO 2012075093A2 US 2011062559 W US2011062559 W US 2011062559W WO 2012075093 A2 WO2012075093 A2 WO 2012075093A2
Authority
WO
WIPO (PCT)
Prior art keywords
omega
fatty acids
pharmaceutical formulation
skin
derived
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2011/062559
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English (en)
Other versions
WO2012075093A3 (fr
Inventor
Nirmal Mulye
David Assoulin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NOSTRUM LABORATORIES Inc
Original Assignee
NOSTRUM LABORATORIES Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by NOSTRUM LABORATORIES Inc filed Critical NOSTRUM LABORATORIES Inc
Priority to EP11845029.5A priority Critical patent/EP2646014A2/fr
Priority to US13/991,020 priority patent/US20140005266A1/en
Publication of WO2012075093A2 publication Critical patent/WO2012075093A2/fr
Anticipated expiration legal-status Critical
Publication of WO2012075093A3 publication Critical patent/WO2012075093A3/fr
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/001—Preparations for care of the lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • This invention pertains to topical skin preparations, such as creams or ointments for application to the skin,
  • a high omega- 3 fatty acid content such as derived
  • Omega- 3 fatty acids are a family of polyunsaturated fatty acids that have a final carbon-carbon double bond in the n-3 position! that is, the third bond from the methyl end of the fatty acid. These fatty acids are nutritionally important in
  • Nutritionally important omega-3 fatty acids include a- linolenic acid (ALA), eicosapentaenoic acid (EPA), and
  • DHA docosahexaenoic acid
  • These fatty acids have an even number of carbon atoms and
  • the human body cannot synthesize omega-3 fatty acids de novo, but it can form long chain 20-carbon unsaturated omega-3 fatty acids (like EPA) and 22-carbon unsaturated omega-3 fatty acids (like DHA) from the "short chain” eighteen- carbon omega-3 fatty acid a-linolenic acid.
  • the short chain omega-3 fatty acids are converted to long chain forms (EPA, DHA) with an efficiency of approximately 5% in men, and at a greater percentage in women.
  • omega-6 fatty acids which are essential closely related chemical analogues that are derived from linoleic acid. Both the omega-3 a-linolenic acid and omega-6 linoleic acid must be obtained from food. Synthesis of the longer omega-3 fatty acids from linolenic acid within the body is competitively slowed by the omega-6 analogues. Thus accumulation of long-chain omega-3 fatty acids in tissues is more effective when they are obtained directly from food or when competing amounts of omega-6 analogs do not greatly exceed the amounts of omega-3 fatty acids.
  • Omega-3 fatty acids can be obtained from a number of sources, including vegetable, animal, and fish oils. Many experts believe that fish oils provide the most beneficial blend of fatty acids. It is believed that fish do not actually produce fatty acid in their bodies, but rather accumulate the oils from either consuming omega-3-containing algae or plankton, or from consuming prey fish that consume omega-3 oils.
  • a number of plant species are also sources of omega-3 fatty acids, particularly in the seed oil, including perilla seeds (Linnaean name Perilla frutescens); chia seeds (Salvia hispanica); flax seed (Linum usitatissimum); lingon berry seeds (Vaccinium vitis-idaea); and rapeseed (Brassica napus).
  • omega-3 fatty acids have important health benefits and are useful for treating certain diseases and medical conditions.
  • arachidonic acid an omega-6 fatty acid
  • arachidonic acid has been implicated in undesirable enhanced inflammatory responses in the arachidonic acid cascade.
  • low omega-3 fatty acid dietary intake is implicated in the so- called “diseases of western civilization” (e.g., Alzheimer's Disease, cancer, asthma, Crohn's disease), that involve inflammatory responses.
  • dietary omega-3 fatty acid supplements have been reported to reduce risk factors for heart disease, including high cholesterol and high blood pressure, lower levels of triglycerides, prevent and treat atherosclerosis, lower
  • omega-3 fatty acid dietary intake include reducing symptoms of lupus, treating psychiatric disorders, preventing and treating several forms of cancer, preventing macular degeneration, and treating arthritis.
  • composition of the oily base are disclosed. As noted below, there is poor absorption into the skin from many ointments, which is a factor addressed in this invention.
  • WO2011/056327 discloses antibacterial activity in oral use of topical preparations
  • This invention provides transdermal formulation containing 5% to about 50% by weight of omega-3 fatty acids, for direct application to the skin, useful for treating medical conditions responsive to omega-3 fatty acid therapy, including psoriasis, dermatitis, lowering triglyerides or LDL cholesterol, raising HDL cholesterol, cancers, and as beauty preparations.
  • the skin preparation may be in the form of a cream, ointment, or balm, such as a deodorant stick or lip balm.
  • omega-3 fatty acids are formulated into an ointment or cream for application directly to the skin of the patient.
  • the omega-3 fatty acids are absorbed directly in to the skin for treatment of dermal diseases, or are absorbed into the blood for treatment and prevention of internal diseases, including cardiovascular conditions, neurological conditions, bone and joint conditions, and certain cancers.
  • the method is of value as a beauty treatment, to restore elasticity and a healthy appearance to skin.
  • the formulation and method may be formulated as an ointment or an emulsion (cream) for application directly to the skin.
  • This invention provides a pharmaceutical
  • omega-3 fatty acids are known to be of therapeutic value.
  • omega-3 fatty acids are absorbed directly in to the skin for treatment of dermal diseases, or are absorbed into the blood for treatment and prevention of internal diseases, including cardiovascular conditions, neurological conditions, bone and joint conditions, and certain cancers.
  • the omega-3 fatty acids for the inventive formulations and methods are derived from a marine species, such as a fish oil or crustacean.
  • a marine species such as a fish oil or crustacean.
  • fish known to have high levels of omega-3 fatty acids include so-called "oily fish” such as salmon, tuna, swordfish, halibut, tilefish, cod fish (including cod liver oil), anchovies, and sardines.
  • crustaceans are also known to have high levels of omega-3 fatty acids, including krill, a crustacean in the Antarctic (the source of krill oil) and the New Zealand green-lipped mussel, (also known as Perna canaliculus). These oils are available in about 15% to over 50% omega-3 fatty acid content by weight.
  • omega-3 fatty acids of the inventive formulations and methods may be derived from a vegetable source, in particular seed oils, including perilla seeds (Linnaean name Perilla frutescens); chia seeds (Salvia
  • the topical formulations of this invention may be formulated as an ointment or a cream. Creams are typically emulsions. Generally, creams are more desirable. The
  • Ointments are greasier and typically are more viscous and have a thicker consistency than a cream emulsion. Creams have a lighter consistency, and absorb into the skin more quickly than ointments, and work better when coverage of large areas is required. The slower absorption and greasier feel of ointments may make them less desirable for application to large areas of the skin.
  • the topical formulations may be oil-based, such as an ointment.
  • ointments may be based on a pharmaceutical compatible oil, such as mineral oil, petrolatum, or a vegetable oil.
  • the formulation may be a water-based emulsion.
  • the emulsion may be a cream.
  • the emulsion may be oil-in-water, or water-in-oil.
  • the oil component may be 15% to 60% by weight of omega-3 fatty acids.
  • the oil phase of the emulsion may be at least 20% omega-3 fatty acids.
  • the creams as disclosed herein minimize greasiness of the omega-3 fatty acid formulations, which may be desirable. Furthermore, where greasiness is minimized, absorption into the skin is greater, since the greasy sensation is caused by oil that is not absorbed into the skin.
  • compositions such as surfactants, penetration enhancers, therapeutic agents, fragrances, and colors may be added to the inventive topical pharmaceutical formulation.
  • a non-ionic surfactant may be used as an
  • emulsifying agent such as polysorbate-80 or stearyl alcohol.
  • the omega-3 fatty acids may be formulated with an antioxidant. This may be particularly important because omega-3 fatty acids are easily oxidized and isomerized, reducing their pharmaceutical effectiveness. For this reason, long term storage of omega-3 fatty acid products can be a problem.
  • an antioxidant for example, butylated hydroxyl anisole (BHA), butylated hydroxyl toluene, or alpha-tocopherol may be added in to the instant formulations.
  • the instant formulations may also contain an absorption enhancer, such as isopropyl myristate, that improves penetration of the active omega-3 fatty acids into the skin.
  • an absorption enhancer such as isopropyl myristate
  • the inventive formulations may include at least about 5% by weight of omega-3 fatty acids EPA, DHA, ALA alone or in combination with each other.
  • the concentration can be made higher, for example about 10%, 20%, 40% or 50% omega-3 fatty acids by weight.
  • the pharmaceutical formulation may be prepared as a balm, such as a deodorant stick.
  • the pharmaceutical formulation may be a
  • inventive formulations are expected to have several uses, including treatment of skin diseases, as beauty skin care products, and as transdermal delivery vehicles for omega-3 fatty acids.
  • the inventive formulations may be used to treat a skin disease, including a dermatitis or a psoriasis condition.
  • a skin disease including a dermatitis or a psoriasis condition.
  • dermatitis is meant a general class of irritated skin conditions typically involving scaly or excessively dry skin. Eczema is sometimes used interchangeably with
  • dermatitis and includes atopic dermatitis, an immune- mediated inflammation of the skin arising from an interaction between genetic and environmental factors.
  • the inventive topical formulations are also expected to be useful as transdermal delivery vehicles for omega-3 fatty acids, targeting internal organs.
  • Omega-3 fatty acids have been shown to have beneficial effects in cardiovascular disease, including lowering elevated triglycerides, LDL cholesterol, and VLDL cholesterol, and increasing levels of HDL cholesterol.
  • Omega-3 fatty acids have also shown promise in the prevention and treatment of certain cancers, particularly breast, colon, and prostate cancer. Omega-3 fatty acids have also shown promise in the treatment and prevention of psychiatric disorders, including depression, mood disorders, and dementia conditions. Omega-3 fatty acids have also shown promise in the treatment and prevention of bone and joint diseases, such as rheumatoid arthritis and osteoporosis.
  • a particular advantage of the inventive topical formulations is that large doses of omega-3 fatty acids can be administered without the need for patients to swallow large amounts of capsules. Besides being inconvenient and simply difficult, oil capsules can cause nausea and stomach upset in many people.
  • the topical dosage forms of the instant invention avoids these problems.
  • the inventive formulations are expected to be useful for the administration of large doses of omega-3 fatty acids that can be absorbed directly through the skin and into the blood stream for internal use.
  • inventive formulations are also expected to be useful as general skin care and beauty preparations. This may include restoring elasticity to the skin of older persons, to provide a more youthful physical appearance.
  • a method of reversing the effect of aging of the skin is provided, by applying a pharmaceutical formulation for application directly to human skin comprising about 10% to 50% by weight of omega-3 fatty acids.
  • the instant topical formulations are useful with animals also, including dogs, cats, and livestock, for which administration of omega-3 fatty acids is believed to be beneficial.
  • inventive formulations may be applied directly to the skin of a mammal, including pets such as dogs, cats, rabbits, or animals such as livestock.
  • Salmon Oil Cream This formula used salmon oil containing 23% omega-3 fatty acids. 4.6 g of the oil contains 1050 mg total omega-3 fatty acids, including EPA, 350 mg, and DHA 450 mg.
  • Emulsification Add the oil phase slowly to the water phase under high speed stirring.
  • the cream is packed into foil tubes under nitrogen.
  • the total omega-3 fatty acid content of this cream is 8.0%.
  • a typical application for a skin condition is
  • omega-3 fatty acids 2 to 4 g applied to an inconspicuous body area, such as the inside of the thighs or inside of the forearms, in a divided dose morning and night.
  • Flax seed oil cream The same formulation used in Example 1 is prepared, but using flax seed oil instead of salmon oil. The flax seed oil contains 55% alpha-linolenic acid. This cream has 19.25% alpha-linolenic acid by weight.
  • This cream has 12.1% omega-3 fatty acids by weight.
  • a high concentration ointment is prepared as follows with salmon oil. [0039] Formula:
  • step 2 Add the product of step 2 to step 1.
  • This ointment is packed into foil tubes under nitrogen.
  • the total omega-3 fatty acid content of this ointment is 13.8%
  • Flax seed oil ointment The ointment of Example 4 iss prepared, substituting flax seed oil for fish oil.
  • the flax seed oil contains 55% alpha-linolenic acid (ALA).
  • the omega-3 content of this oil (ALA) is 33%.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une forme pharmaceutique, destinée à être directement appliquée sur la peau humaine et comprenant environ 5 à 50 % en poids d'acides gras oméga-3 issus d'huile de poisson ou d'origine végétale. Ladite forme galénique peut correspondre à une pommade ou à une émulsion aqueuse. Ladite forme galénique peut être utilisée pour le traitement de maladies cutanées, d'affections cardiovasculaires, ainsi que comme produit de soin de la peau ou de beauté en général, ayant un effet anti-âge sur la peau.
PCT/US2011/062559 2010-12-01 2011-11-30 Formes galéniques topiques utilisables en vue de l'administration d'acides gras oméga-3 Ceased WO2012075093A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11845029.5A EP2646014A2 (fr) 2010-12-01 2011-11-30 Formes galéniques topiques utilisables en vue de l'administration d'acides gras oméga-3
US13/991,020 US20140005266A1 (en) 2010-12-01 2011-11-30 Topical formulations for administration of omega-3 fatty acids

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US41870510P 2010-12-01 2010-12-01
US61/418,705 2010-12-01
US42226410P 2010-12-13 2010-12-13
US61/422,264 2010-12-13

Publications (2)

Publication Number Publication Date
WO2012075093A2 true WO2012075093A2 (fr) 2012-06-07
WO2012075093A3 WO2012075093A3 (fr) 2014-04-10

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Country Link
US (1) US20140005266A1 (fr)
EP (1) EP2646014A2 (fr)
WO (1) WO2012075093A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013150384A1 (fr) * 2012-04-04 2013-10-10 Pronova Biopharma Norge As Compositions comprenant des acides gras oméga-3 et de la vitamine d destinées à lutter contre le psoriasis, et méthodes et utilisations associées
WO2022098880A1 (fr) * 2020-11-05 2022-05-12 Ambo Innovations Llc Formulation topique comprenant des acides gras oméga-3, de la mélatonine et de la vitamine d
WO2023205207A1 (fr) * 2022-04-19 2023-10-26 Omeza Holdings, Inc. Compositions topiques pour réduire la cicatrisation
WO2023220273A1 (fr) * 2022-05-11 2023-11-16 Ambo Innovations Llc Formulation topique comprenant des acides gras oméga-3, de la mélatonine et de la vitamine d

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9486476B2 (en) * 2014-08-05 2016-11-08 Natures Products, Inc Fast acting joint relief formulations

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AU8083691A (en) * 1990-05-07 1991-11-27 Barry I. Bockow Methods and preparations of stable, deodorized oils and pharmaceutical compositions thereof
US6967023B1 (en) * 2000-01-10 2005-11-22 Foamix, Ltd. Pharmaceutical and cosmetic carrier or composition for topical application
US20060251685A1 (en) * 2003-03-18 2006-11-09 Zhi-Jian Yu Stable ophthalmic oil-in-water emulsions with Omega-3 fatty acids for alleviating dry eye
DE102004049062A1 (de) * 2004-03-30 2005-10-13 bitop Aktiengesellschaft für biotechnische Optimierung Topische Zubereitung zur Anwendung auf der Haut enthaltend natürliches Öl der Nachtkerze (Oenothera biennis) (=Oleum Oenothera) und Osmolyte aus extremophilen Mikroorganismen
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KR100652650B1 (ko) * 2004-07-28 2006-12-06 엘지전자 주식회사 서비스 음영지역에서 동기화를 위한 피티티 서비스 시스템및 방법
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013150384A1 (fr) * 2012-04-04 2013-10-10 Pronova Biopharma Norge As Compositions comprenant des acides gras oméga-3 et de la vitamine d destinées à lutter contre le psoriasis, et méthodes et utilisations associées
US9585896B2 (en) 2012-04-04 2017-03-07 Pronova Biopharma Norge As Compositions comprising omega-3 fatty acids and vitamin D for psoriasis, and methods and uses thereof
WO2022098880A1 (fr) * 2020-11-05 2022-05-12 Ambo Innovations Llc Formulation topique comprenant des acides gras oméga-3, de la mélatonine et de la vitamine d
WO2023205207A1 (fr) * 2022-04-19 2023-10-26 Omeza Holdings, Inc. Compositions topiques pour réduire la cicatrisation
WO2023220273A1 (fr) * 2022-05-11 2023-11-16 Ambo Innovations Llc Formulation topique comprenant des acides gras oméga-3, de la mélatonine et de la vitamine d

Also Published As

Publication number Publication date
EP2646014A2 (fr) 2013-10-09
US20140005266A1 (en) 2014-01-02
WO2012075093A3 (fr) 2014-04-10

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